50546-23-1Relevant academic research and scientific papers
Enantioselective organocatalytic synthesis of 2-oxopiperazines from aldehydes: Identification of the elusive epoxy lactone intermediate
Kaplaneris, Nikolaos,Spyropoulos, Constantinos,Kokotou, Maroula G.,Kokotos, Christoforos G.
supporting information, p. 5800 - 5803 (2016/11/29)
An organocatalytic linchpin catalysis approach was envisaged to convert simple aldehydes into enantioenriched 2-oxopiperazines. A four-step reaction sequence (chlorination, oxidation, substitution, and cyclization) was developed and led to different substitution patterns in high yields and selectivities. The reaction mechanism was studied, and the previously elusive epoxy lactone intermediate was identified by HRMS.
Iridium-catalyzed 1,3-hydrogen shift/chlorination of allylic alcohols
Ahlsten, Nanna,Gomez, Antonio Bermejo,Martin-Matute, Belen
supporting information, p. 6273 - 6276 (2013/07/05)
Tandem: Allylic alcohols react with N-chlorosuccinimide (NCS) in a tandem 1,3-H shift/C-Cl bond formation leading to α-chloroketones and α-chloroaldehydes. The reactions proceed with complete selectivity to give single constitutional isomers of monochlorinated carbonyl compounds. The utility of the transformation is illustrated by the straightforward synthesis of 4,5-disubstituted 2-aminothiazoles from allylic alcohols. Copyright
Enantioselective synthesis of C2-functionalized, N-protected morpholines and orthogonally N,N′-protected piperazines via organocatalysis
O'Reilly, Matthew C.,Lindsley, Craig W.
experimental part, p. 1539 - 1542 (2012/04/10)
In this Letter, we describe a novel three-step, one-pot procedure for the enantioselective synthesis of N-benzyl protected morpholines and orthogonally N,N′-protected piperazines with chiral alkyl groups installed at the C2 position of each heterocyclic c
